3-Naphtho[2,3-d][1,3]dioxol-5-yl-propionic acid ethyl ester | 152560-90-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-Naphtho[2,3-d][1,3]dioxol-5-yl-propionic acid ethyl ester
• CAS: 152560-90-2
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: CVQJYOJIAPAOMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-Naphtho[2,3-d][1,3]dioxol-5-yl-propionic acid ethyl ester 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以95%的产率得到3-Naphtho[2,3-d][1,3]dioxol-5-yl-propionic acid
  参考文献：
  名称：

  An unusual trimethylsilyltriflate catalyzed transformation of 6-[3-aryl-2-hydroxypropyl]-4,5-dihydro-3(2-pyridazinones into 3-(1-naphthyl)propionic acid esters

  摘要：

  Treatment of 6-(3-phenyl-2-hydroxypropyl)4,5-dihydro-3(2H)-pyridazinones 6a-c with trimethylsilyl triflate (TMST) in refluxing dichloromethane gave the unexpected 3-(1-naphthyl)propionic acid ethyl ester derivatives 9a-c. The isolation of the spirotetrahydropyridazinone intermediate 5 suggests, as a plausible reaction mechanism, an intramolecular aminoalkylation key step, followed by ring opening and elimination of hydrazine and water also promoted by TMST.

  DOI：

  10.1016/s0040-4039(00)79226-4
• 作为产物：
  描述：

  乙醇 、 6-(3-Benzo[1,3]dioxol-5-yl-2-trimethylsilanyloxy-propyl)-4,5-dihydro-2H-pyridazin-3-one 在 三氟甲磺酸三甲基硅酯 作用下， 以 1,2-二氯乙烷 为溶剂， 以70%的产率得到3-Naphtho[2,3-d][1,3]dioxol-5-yl-propionic acid ethyl ester
  参考文献：
  名称：

  An unusual trimethylsilyltriflate catalyzed transformation of 6-[3-aryl-2-hydroxypropyl]-4,5-dihydro-3(2-pyridazinones into 3-(1-naphthyl)propionic acid esters

  摘要：

  Treatment of 6-(3-phenyl-2-hydroxypropyl)4,5-dihydro-3(2H)-pyridazinones 6a-c with trimethylsilyl triflate (TMST) in refluxing dichloromethane gave the unexpected 3-(1-naphthyl)propionic acid ethyl ester derivatives 9a-c. The isolation of the spirotetrahydropyridazinone intermediate 5 suggests, as a plausible reaction mechanism, an intramolecular aminoalkylation key step, followed by ring opening and elimination of hydrazine and water also promoted by TMST.

  DOI：

  10.1016/s0040-4039(00)79226-4